Your browser doesn't support javascript.
loading
Syntheses of (-)-Tripterifordin and (-)-Neotripterifordin from Stevioside.
Kobayashi, Shoji; Shibukawa, Keisuke; Hamada, Yoshiki; Kuruma, Takuma; Kawabata, Asako; Masuyama, Araki.
Afiliação
  • Kobayashi S; Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
  • Shibukawa K; Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
  • Hamada Y; Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
  • Kuruma T; Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
  • Kawabata A; Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
  • Masuyama A; Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
J Org Chem ; 83(3): 1606-1613, 2018 02 02.
Article em En | MEDLINE | ID: mdl-29328659
ABSTRACT
We report short syntheses of (-)-tripterifordin and (-)-neotripterifordin, potent inhibitors of HIV replication, from stevioside, a natural sweetener used worldwide. The key transformations are reduction at C13 through the formation of a tertiary chloride and subsequent three-step lactonization including a selective iodination at C20 by the photoreaction of the C19-alcohol. The title compounds were reliably obtained from stevioside in 9 and 11 steps (with 5-7 isolation steps), respectively. Additionally, the related lactone-containing ent-kaurenes, doianoterpenes A and B, and two more natural products were synthesized.
Assuntos
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Diterpenos do Tipo Caurano / Diterpenos / Glucosídeos Idioma: En Revista: J Org Chem Ano de publicação: 2018 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Diterpenos do Tipo Caurano / Diterpenos / Glucosídeos Idioma: En Revista: J Org Chem Ano de publicação: 2018 Tipo de documento: Article